Why Carlito's Way Is the Most Underrated Gangster Movie

And maybe the one with the most heart

For twenty years I've been re-watching the same film, often re-enacting scenes in my head as if I were headlining a one-man show — a feat I'd pull off if not for the elephant tears I'd be shedding all over the stage. Calling a film your "favorite" is a weird thing. Hell, ranking in general makes me uneasy. I mean, how can I ever say any film is the best when we live in a world where Jaws exists? Yet here I am, shouting it for all to read: I fking love Carlito's Way, which this week has its twentieth anniversary... and it could be my favorite movie.

Yet I can't help but think that this gold crown of a flick has gotten the short end of the popular stick. How could this happen? One word, two syllables: Scarface. Carlito's Way will always be the younger sibling to the king of coked-up gangster cinema. Right now you can buy Scarface rugs. No one makes rugs with Carlito on it... unless I special-order it.

The comparisons between the two are apt considering that Carlito's Way was another gangster film featuring the re-teaming of director Brian De Palma and Al Pacino — and made just ten years after Scarface. The pictures also feature overlapping cast members, as well as other bits of trivia connecting them that you can easily Google. Yet there's a Grand Canyon-sized chasm between them, for as much as Scarface is cold and harsh throughout its nearly three-hour running time, Carlito's Way wears its beating heart on its sleeve for all of its tight two-plus hours.

And Carlito's Way is all about time. Its protagonist, Carlito Brigante, is released into the world after a prison stint and earnestly wants to go clean, yet nearly every old haunt and pal are knocking him further down the lawless ladder. When it finally looks as if he's lined everything up for a life in the islands, his internal stopwatch starts and doesn't end until he gets shot in the finale. Oh, did I spoil that? Well, guess what, I didn't, because the film starts with him getting shot and then rewinds to fill in what leads up to that, so take a pill and deal with it.

No ifs, ands, buts about it — Carlito's Way is a tragedy. The film's somber mood is balanced only by its larger-than-life performances, retro '70s threads, thrilling sequences, and plenty of sweaty disco tunes outside of Patrick Doyle's stellar score. But boy, does it have heart! Pacino's eyes tell a story all their own — and they're not filled with his now-stereotypical "Hooo Ahhhs" that earned him that Scent of a Woman Academy Award just one year prior (something which inevitably stained Carlito's critical reaction at the time). Instead, Pacino turns in a riveting performance that's mostly understated, but busted wide open by some of the best bravura scenes of his career — take the scene where he's cornered in a bathroom with a gun and no bullets and hollers his way out of a deadly situation by talking the sickest smack you've ever heard. Later he goes from zero to intense during a domestic argument as he smashes a mirror while sticking up for his code of honor, which includes a loyalty to his friends that will inevitably get him killed — his girlfriend even says so!

And let's talk about his friends — first off, Davey Kleinfeld, one of the best coked-up characters in cinema history. That horrendous perm of his helps disguise bad-boy actor Sean Penn, who, in a totally awesome alternate universe, would have won an Oscar for this — or at least been nominated. He's Carlito's number-one dude, the lawyer who got him out of prison and is bound to get him into more trouble. Then there's Luis Guzman's Pachanga, another brother from the past who's in it for himself behind his boss's back. Now there are some buddies Carlito sees right through, like Lalin, the wheelchair-bound ex-con who Pacino catches wearing a wire. Played to the hilt by Viggo Mortensen (looong before he won hearts in Middle Earth), Lalin has just minutes of screentime, but levels the playing field with a performance that couldn't be more different from the quiet cool that he's known for now. The entire world should stop what they are doing and slow-clap every time his monologue is played about having to wear diapers, trust me.

And then there's Gail... You see, Carlito's Way is — beyond the foot chases, the insane De Palma camera direction, and a career-making moment by John Leguizamo as Benny Blanco from the Bronx — at its heart a romance. Gail (played by Penelope Ann Miller) is Carlito's angel, the dancer ex-girlfriend he pined for while in the joint and spies on in the rain when he gets out. There are some who claim that she's the weak link in the cast, but I find no wrong in the performance. Her character could be richer just like my belly should have abs.

But this isn't Gail's Way, it's Carlito's — and he is one damn fine character played by one of the best in the biz. Culled from real-life judge Edwin Torres's two novels inspired by the colorful characters on the streets while he was growing up, Carlito isn't searching for redemption as much as yearning for a way out. And he believes that he can do it — and you want to believe he can, too. You want him to hitch a ride with Gail at the end of the film and go rent cars down south under a thatched roof, which makes his journey all the more intense.

And boy howdy, is this film packed with tension! Take the pool scene — expertly choreographed, with Carlito keeping an eye on his cousin by staging an elaborate billiards trick that includes the reflection of a killer in another thug's aviator shades. Or the entire finale chase, which starts at the disco club (an incredible set in and of itself) and stretches through the streets, onto a train, then into Grand Central. If not for Kathryn Bigelow's Point Break, it'd be considered the French Connection of foot chases.

And here's where I get sorta specific, so turn away if you must. But just when things look good for our man Charlie, the rug is pulled out from under him. After every angle Carlito ran through in his head... all the hoods he dodged... he misses one thing — the same pompous attitude that landed him in jail comes to shoot him point blank by way of another street hood whom he let live when he really shouldn't have. And this horrible moment happens in front of Gail, who called it just scenes before, but was blinded by Carlito's charismatic belief that everything would work out.

And then the film comes to its heartbreaking close, re-enacting the brilliant camera move that opens the picture. Carlito is on the gurney and the audience gets one final inner monologue from him as he closes up shop on this world. He stares at a travel sign and envisions Gail dancing on the beach with the money he gave her — and the camera closes in on those sparkling Pacino eyes. When they finally close, the end credits roll to Joe Cocker's "You Are So Beautiful" as Gail dances against a sunset. It's a powerful moment — yet you have to stay through the rolling credits to see the one final gut punch — the thing that nails the film's landing, for just as Cocker's voice cracks in only the way it does, we see little baby Carlito run into the frame as Gail snatches him up and dances to a fade out. World, I'm gonna need one more slow-clap from y'all. And maybe some tissues.

Carlito's Way survived its initial critical reception and has only gained admiration as the years go by. In 2005 a direct-to-video prequel was made and is horrible. Luis Guzman co-starred in it playing a different dude. The character of Lalin did not make an appearance, much to the dismay of this writer.

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Jeremy Wheeler is a writer/illustrator based in Ann Arbor, MI, who has contributed to the All Movie Guide, Chicago Reader, A.V. Club, and others. He's also the poster designer for Bang! Media.

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